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(4R)-Ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate

The title compound, C(21)H(17)ClO(6), is optically pure and adopts an R configuration. It was obtained by an organocatalytic asymmetric Michael addition of 4-hydroxy­coumarin with (E)-ethyl 4-(4-chloro­phen­yl)-2-oxobut-3-enoate. The structure consists of a tetra­hydro­pyran unit fused to the coumar...

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Detalles Bibliográficos
Autores principales: Wang, Yifeng, Zhang, Wei, Xu, Xiangsheng, Zhang, Guangcun
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980058/
https://www.ncbi.nlm.nih.gov/pubmed/21580101
http://dx.doi.org/10.1107/S1600536809051976
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author Wang, Yifeng
Zhang, Wei
Xu, Xiangsheng
Zhang, Guangcun
author_facet Wang, Yifeng
Zhang, Wei
Xu, Xiangsheng
Zhang, Guangcun
author_sort Wang, Yifeng
collection PubMed
description The title compound, C(21)H(17)ClO(6), is optically pure and adopts an R configuration. It was obtained by an organocatalytic asymmetric Michael addition of 4-hydroxy­coumarin with (E)-ethyl 4-(4-chloro­phen­yl)-2-oxobut-3-enoate. The structure consists of a tetra­hydro­pyran unit fused to the coumarin ring ring system. The hydroxyl and phenyl groups are on the same side of the tetra­hydro­pyrane ring. The benzene ring is almost perpendicular to the coumarin ring [dihedral angle of 72.89 (3)°]. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds are observed. An intra­molecular O—H⋯O contact also occurs.
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spelling pubmed-29800582010-12-30 (4R)-Ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate Wang, Yifeng Zhang, Wei Xu, Xiangsheng Zhang, Guangcun Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(21)H(17)ClO(6), is optically pure and adopts an R configuration. It was obtained by an organocatalytic asymmetric Michael addition of 4-hydroxy­coumarin with (E)-ethyl 4-(4-chloro­phen­yl)-2-oxobut-3-enoate. The structure consists of a tetra­hydro­pyran unit fused to the coumarin ring ring system. The hydroxyl and phenyl groups are on the same side of the tetra­hydro­pyrane ring. The benzene ring is almost perpendicular to the coumarin ring [dihedral angle of 72.89 (3)°]. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds are observed. An intra­molecular O—H⋯O contact also occurs. International Union of Crystallography 2009-12-19 /pmc/articles/PMC2980058/ /pubmed/21580101 http://dx.doi.org/10.1107/S1600536809051976 Text en © Wang et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Wang, Yifeng
Zhang, Wei
Xu, Xiangsheng
Zhang, Guangcun
(4R)-Ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate
title (4R)-Ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate
title_full (4R)-Ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate
title_fullStr (4R)-Ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate
title_full_unstemmed (4R)-Ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate
title_short (4R)-Ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate
title_sort (4r)-ethyl 4-(4-chloro­phen­yl)-2-hydr­oxy-5-oxo-2,3,4,5-tetra­hydro­pyrano[3,2-c]chromene-2-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2980058/
https://www.ncbi.nlm.nih.gov/pubmed/21580101
http://dx.doi.org/10.1107/S1600536809051976
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